EF5

EF5
IUPAC name

2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Other names

NSC-684681; EF-5
Identifiers
CAS number 152721-37-4 Y
PubChem 389053
ChemSpider 344807 Y
UNII 383HJ2T87O Y
Jmol-3D images Image 1
Properties
Molecular formula C8H7F5N4O3
Molar mass 302.16 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

EF5 is a nitroimidazole used in oncology research.[1] Due to its similarity in chemical structure to etanidazole, EF5 binds in cells displaying hypoxia.[2]

The 18F-radiolabeled derivative of EF5 is being studied for its possibility to be used in positron emission tomography (PET) to detect low levels of oxygen in brain tumors.[3] This can help show how a tumor will respond to treatment.

References

  1. ^ Evans, Sydney M.; Fraker, Douglas; Hahn, Stephen M.; Gleason, Kristen; Jenkins, W. Timothy; Jenkins, Kevin; Hwang, Wei-Ting; Zhang, Paul; Mick, Rosemarie; Koch, Cameron J (2006). "EF5 binding and clinical outcome in human soft tissue sarcomas". International Journal of Radiation Oncology, Biology, Physics 64 (3): 922–927. doi:10.1016/j.ijrobp.2005.05.068. 
  2. ^ Lord, Edith M.; Harwell, Lee; Koch, Cameron J. (1993). "Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts". Cancer Research 53 (23): 5721–5726. PMID 8242628. 
  3. ^ Ziemer, L. S.; Evans, S. M.; Kachur, A. V.; Shuman, A. L.; Cardi, C. A.; Jenkins, W. T.; Karp, J. S.; Alavi, A.; Dolbier, W. R.; Koch, C. J. (2003). "Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5". European Journal of Nuclear Medicine and Molecular Imaging 30 (2): 259–266. doi:10.1007/s00259-002-1037-5. PMID 12552344.